JPH07121966B2 - Controlled rheology polypropylene - Google Patents
Controlled rheology polypropyleneInfo
- Publication number
- JPH07121966B2 JPH07121966B2 JP62502556A JP50255687A JPH07121966B2 JP H07121966 B2 JPH07121966 B2 JP H07121966B2 JP 62502556 A JP62502556 A JP 62502556A JP 50255687 A JP50255687 A JP 50255687A JP H07121966 B2 JPH07121966 B2 JP H07121966B2
- Authority
- JP
- Japan
- Prior art keywords
- polypropylene
- peroxide
- peroxide compound
- molecular weight
- ppm
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/50—Partial depolymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/10—Chemical modification of a polymer including a reactive processing step which leads, inter alia, to morphological and/or rheological modifications, e.g. visbreaking
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
Description
【発明の詳細な説明】 技術分野 本発明は、分子量を減少させおよび抽出の間ポリプロピ
レンの分子量分布の制限を伴なう第三ブチルアルコール
（TBA）の除去に関する。Description: TECHNICAL FIELD The present invention relates to the removal of tert-butyl alcohol (TBA) with a reduction in molecular weight and a restriction of the molecular weight distribution of polypropylene during extraction.
有機過酸化物を溶融相中でポリプロピレンと混合した場
合、このポリマーが低分子量に分解する原因となる。ま
た得られるポリプロピレンは、出発物質よりせまい分子
量分布を有し、最終プラスチック生成物の二次加工の
間、改良された流動性を示す。有機過酸化物の存在下で
製造される市販ポリプロピレンは、制御レオロジー（C
R）樹脂として公知である。多くの種類の過酸化物が利
用できるが、その特有の分解温度のため、特定の過酸化
物〔2,5−ジメチル−2,5−ビス（ｔ−ブチルペルオキ
シ）ヘキサン〕が、CRポリマーを製造する産業において
選択された過酸化物である。ルシドールディビジョンオ
ブペンワルトコープ（Lucidol Division of Pennwalt C
orp.）により販売されているルペンソール（Lupersol）
101は、そのような過酸化物である。When an organic peroxide is mixed with polypropylene in the melt phase, it causes the polymer to decompose to a low molecular weight. The resulting polypropylene also has a narrower molecular weight distribution than the starting material and exhibits improved flowability during fabrication of the final plastic product. Commercially available polypropylene produced in the presence of organic peroxide has controlled rheology (C
R) Known as resin. Although many types of peroxides are available, certain peroxides [2,5-dimethyl-2,5-bis (t-butylperoxy) hexane] give CR polymers because of their unique decomposition temperatures. It is the peroxide of choice in the manufacturing industry. Lucidol Division of Pennwalt C
Lupersol sold by orp.)
101 is such a peroxide.
ルペルソール101で製造されたCR樹脂は、良好な加工性
を示すけれども、この樹脂は異なる量のTBAを含む。加
熱した場合、これらの樹脂はTBAの不快な臭気を放出す
る。また、政府の規制により、最近ポリプロピレン樹脂
または生成物中に存在するTBAの量が25ppmに制限され
た。Although the CR resin made with Lupersol 101 shows good processability, it contains different amounts of TBA. When heated, these resins give off the unpleasant odor of TBA. Also, government regulations have recently limited the amount of TBA present in polypropylene resins or products to 25 ppm.
背景技術 本発明以前、ポリプロピレンの加工性は、その製造後、
少量の過酸化物化合物をポリプロピレンに混入すること
により改良されることは公知であった。この過酸化物化
合物は、典型的には押出機に入れられる前に、時には不
活性ガス中でポリプロピレン粒子またはペレットに加え
られ、加熱および／またはスクリューあるいはミキサー
の機械エネルギーによって溶融され、制御された、予言
できる流動特性を有するペレット、フィルム、あるいは
シートに押出される。Background Art Prior to the present invention, the processability of polypropylene is
It was known to be improved by incorporating small amounts of peroxide compounds into polypropylene. This peroxide compound was typically added to polypropylene particles or pellets, sometimes in an inert gas, before being placed in an extruder, melted and controlled by heating and / or mechanical energy of a screw or mixer. , Extruded into pellets, films, or sheets with predictable flow characteristics.
過酸化物化合物は、遊離基開始剤として米国特許第3,14
4,436号を参照し、この特許において、それらは押出機
中の生成物のメルトインデックスを改良するため用いら
れる。Peroxide compounds have been described as free radical initiators in US Pat.
With reference to 4,436, in this patent they are used to improve the melt index of the product in the extruder.
脂肪族過酸化物は、米国特許第3,887,534号において結
晶ポリプロピレン粉末と共に用いられ、固有粘度および
溶融流れを改良する。Aliphatic peroxides have been used with crystalline polypropylene powder in US Pat. No. 3,887,534 to improve intrinsic viscosity and melt flow.
米国特許第3,940,379号において、ポリエチレンの制御
された酸化分解は、他の過酸化物の使用により行なわ
れ、この特許は、最小の酸化分解と共に最小の熱分解で
得られる生成物の本質的に色および臭気のない特性を強
調している。In U.S. Pat.No. 3,940,379, the controlled oxidative degradation of polyethylene is carried out by the use of other peroxides, which patent describes essentially the color of the product obtained with minimal oxidative degradation and minimal thermal degradation. And emphasizes its odorless properties.
多くの特許は、過酸化物の使用によるポリエチレンの架
橋を教示している−米国特許第3,846,396号、第3,917,7
45号および第3,963,673号参照。Many patents teach the crosslinking of polyethylene by the use of peroxides-U.S. Pat.Nos. 3,846,396, 3,917,7.
See 45 and 3,963,673.
我々が用いる過酸化物化合物の１種である3,6,6,9,9−
ペンタメチル−３−ｎ−プロピル−1,2,4,5−テトラオ
キサシクロノナンは、架橋ポリプロピレンに有効である
と米国特許第4,271,279号に開示された過酸化物の群の
一般式に含まれる。この一般式の化合物は、プロピレン
コポリマーの加工性の改良に有効である、米国特許第4,
451,589号に示されている。One of the peroxide compounds we use is 3,6,6,9,9-
Pentamethyl-3-n-propyl-1,2,4,5-tetraoxacyclononane is included in the general formula of the group of peroxides disclosed in US Pat. No. 4,271,279 as being effective in cross-linked polypropylene. Compounds of this general formula are effective in improving the processability of propylene copolymers, US Pat.
It is shown in No. 451,589.
読者は、過酸化物の処理によるエチレンコポリマーの透
明フィルムの生成を示す米国特許第4,460,750号に関心
があるであろう。The reader will be interested in U.S. Pat. No. 4,460,750 which shows the treatment of peroxides to produce transparent films of ethylene copolymers.
発明の開示 TBAを出す多くの従来技術の過酸化物添加物の一般式傾
向は、我々の発明を用いることにより排除される。つま
りポリプロピレンの加工特性を改良するため用いられる
特定の過酸化物は、望む半減期を有し、およびTBAを形
成しないで制御された方法で、ポリプロピレンを分解す
る能力のため選択される。DISCLOSURE OF THE INVENTION The general formula tendency of many prior art peroxide additives to give TBA is eliminated by using our invention. That is, the particular peroxide used to improve the processing properties of polypropylene has a desired half-life and is selected for its ability to degrade polypropylene in a controlled manner without forming TBA.
本発明は、過酸化物分解によるCRポリマーの製造の間TB
Aの形成を排除する。この方法は、空気の存在または非
存在下で行なわれる。また、この生成物は、ルペルソー
ル101で製造された樹脂と比較して、良好な色および等
しい加工性並びに物理特性を示す。これは、2,2−ジ
（ｔ−アミル）ペルオキシプロパン（ルシドールのルペ
ルソール553）または3,6,6,9,9−ペンタメチル−３−ｎ
−プロピル−1,2,4,5−テトラオキサシクロノナン（ペ
ルオキシジョンディビジョンオブウィコケミのエスペラ
ル529）を用いることによって行なわれる。The present invention provides TB during the production of CR polymers by peroxide decomposition.
Eliminate the formation of A. The method is carried out in the presence or absence of air. The product also exhibits good color and equal processability and physical properties as compared to the resin made with Lupersol 101. This is 2,2-di (t-amyl) peroxypropane (lupersol 553 of lucidol) or 3,6,6,9,9-pentamethyl-3-n.
-Propyl-1,2,4,5-tetraoxacyclononane (Esperal 529 of Peroxy John Division of Wicochem).
本発明の方法において、公知量の過酸化物が窒素下従来
の添加物または安定剤を含むポリプロピレン粉末とあら
かじめ混合される。我々の発明が有効であるポリプロピ
レンは、最大10％エチレンを有するコポリマーを含む。
このポリプロピレン／過酸化物混合物は、窒素パージ
下、ミキサーまたは押出機に加えられ、混合しながら18
0℃に予備加熱される。In the process of the present invention, a known amount of peroxide is premixed under nitrogen with a polypropylene powder containing conventional additives or stabilizers. The polypropylenes for which our invention is useful include copolymers with up to 10% ethylene.
The polypropylene / peroxide mixture was added to a mixer or extruder under a nitrogen purge and mixed with mixing 18
Preheated to 0 ° C.
我々の過酸化物物質は、50〜10,000ppmの濃度でポリプ
ロピレンペレット、フレークまたは粉末に加えるべきで
ある。この成分（ポリプロピレン粉末、過酸化物、およ
び添加物）を、室温でおよび次いで押出機中550゜Fを越
えない温度で予備混合し、またはポリプロピレン粉末並
びに添加物を室温で予備混合し、過酸化物と共に押出機
に同時に加え、あるいはすべての成分を押出機に加える
前に550゜Fを越えない加熱ミキサー中で予備混合する。
この混合は350〜550゜Fで行なうべきである。Our peroxide material should be added to polypropylene pellets, flakes or powders at concentrations of 50-10,000 ppm. This component (polypropylene powder, peroxide, and additives) is premixed at room temperature and then in an extruder at a temperature not exceeding 550 ° F, or polypropylene powder and additives are premixed at room temperature and peroxide The ingredients are either added to the extruder at the same time, or all ingredients are premixed in a heated mixer not exceeding 550 ° F prior to addition to the extruder.
This mixing should occur at 350-550 ° F.
我々の物質は、128℃で1.0〜10時間の半減期を有する過
酸化物化合物であり、これはTBAに分解しない。これ
は、上述の押出条件下で過酸化物物質がポリプロピレン
中に残らないことを意味する。特に、我々の物質は、2,
2−ジ（ｔ−アミル）ペルオキシプロパンおよび3,6,6,
9,9−ペンタメチル−3n−プロピル−1,2,4,5−テトラオ
キサシクロノナンを含む群より選ばれる。バンバリーミ
キサーを20rpmで用い、すべてのサンプルを加えた場
合、混合速度を80rpmに増加し、および10kgラム重量下
で180℃において１〜３分間混合を続ける。この時間の
終りに、窒素下物質を移し、冷却し、粉末に砕く。この
方法を行った場合、比較分子量およびTBA含量を、サン
プルについて測定した。結果を表Ｉに示す。Our material is a peroxide compound with a half-life of 1.0-10 hours at 128 ° C, which does not decompose to TBA. This means that no peroxide material remains in the polypropylene under the extrusion conditions described above. In particular, our material is 2,
2-di (t-amyl) peroxypropane and 3,6,6,
It is selected from the group comprising 9,9-pentamethyl-3n-propyl-1,2,4,5-tetraoxacyclononane. When using a Banbury mixer at 20 rpm, if all samples were added, increase the mixing speed to 80 rpm and continue mixing at 180 ° C. under 10 kg ram weight for 1-3 minutes. At the end of this time, transfer the material under nitrogen, cool and grind to a powder. When this method was performed, comparative molecular weight and TBA content were measured on the samples. The results are shown in Table I.
同様のテストを１インチのイエロージャケット押出機中
で行ない、得られた結果を表IIに示す。 Similar tests were conducted in a 1 inch yellow jacket extruder and the results obtained are shown in Table II.
この結果は、同じ濃度においてルペルソール553はルペ
ルソール101ほど効果的でないことを示しているが、こ
のシステムよりTBAを完全に除去すると、ルペルソール5
53の濃度を増加させるかもしれない。 The results show that at the same concentration, lupersol 553 was not as effective as lupersol 101, but when TBA was completely removed from this system, lupersol 5
May increase the concentration of 53.
表IIIおよび表IVは、他の２種類の押出機で集めたデー
タを示す。Tables III and IV show the data collected on the other two extruders.
Claims (8)
れる、ポリプロピレンの加工特性の改良方法において、
128℃において、約１〜約10時間の半減期を有し、ｔ−
ブチルアルコールにポリプロピレンを分解しない過酸化
物化合物を約50〜10,000ppm加え、この混合物を熱機械
作用下溶融させ、過酸化物化合物およびｔ−ブチルアル
コールを有しない固体ポリプロピレン生成物を形成する
ことを含んでなり、それによりポリプロピレン生成物の
分子量が減少し、溶融流れが増加し、分子量分布が狭く
なる改良方法。1. A method of improving the processing properties of polypropylene, wherein the peroxide compound is mixed with polypropylene,
It has a half-life of about 1 to about 10 hours at 128 ° C, and t-
About 50 to 10,000 ppm of a peroxide compound that does not decompose polypropylene is added to butyl alcohol and the mixture is melted under thermomechanical action to form a solid polypropylene product free of peroxide compound and t-butyl alcohol. An improved process which comprises reducing the molecular weight of the polypropylene product, increasing the melt flow and narrowing the molecular weight distribution.
る、請求の範囲第１項記載の方法。2. A method according to claim 1 wherein the thermomechanical action is performed at about 330-550 ° F.
る、請求の範囲第１項記載の方法。3. The method of claim 1 wherein the thermomechanical action is performed at about 350-500 ° F.
れる、請求の範囲第１項記載の方法。4. The method of claim 1 wherein the peroxide compound is mixed at about 40-500 ppm.
請求の範囲第１項記載の方法。5. The polypropylene product is pellets.
The method according to claim 1.
を含む、請求の範囲第１項記載の方法。6. The method of claim 1 wherein the polypropylene comprises up to about 10% ethylene.
オキシプロパンである、請求の範囲第１項記載の方法。7. The method according to claim 1, wherein the peroxide is 2,2-di (t-amyl) peroxypropane.
n−プロピル−1,2,4,5−テトラオキサシクロノナンであ
る、請求の範囲第１項記載の方法。8. A peroxide is 3,6,6,9,9-pentamethyl-3.
The method of claim 1 which is n-propyl-1,2,4,5-tetraoxacyclononane.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US860356 | 1986-05-06 | ||
| US06/860,356 US4707524A (en) | 1986-05-06 | 1986-05-06 | Controlled-rheology polypropylene |
| PCT/US1987/000852 WO1987006944A1 (en) | 1986-05-06 | 1987-04-17 | Controlled-rheology polypropylene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63503228A JPS63503228A (en) | 1988-11-24 |
| JPH07121966B2 true JPH07121966B2 (en) | 1995-12-25 |
Family
ID=25333043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62502556A Expired - Lifetime JPH07121966B2 (en) | 1986-05-06 | 1987-04-17 | Controlled rheology polypropylene |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4707524A (en) |
| EP (1) | EP0270570A1 (en) |
| JP (1) | JPH07121966B2 (en) |
| WO (1) | WO1987006944A1 (en) |
| ZA (1) | ZA873001B (en) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047485A (en) * | 1989-02-21 | 1991-09-10 | Himont Incorporated | Process for making a propylene polymer with free-end long chain branching and use thereof |
| US5017661A (en) * | 1990-02-12 | 1991-05-21 | Phillips Petroleum Company | Process for reducing the level of t-butyl alcohol (TBA) in visbroken polyolefins |
| US5198506A (en) * | 1991-05-10 | 1993-03-30 | Phillips Petroleum Company | High organic peroxide content polypropylene |
| USH1375H (en) * | 1991-10-15 | 1994-11-01 | Shell Oil Company | Polyketone polymer blends |
| US5368919A (en) * | 1993-05-20 | 1994-11-29 | Himont Incorporated | Propylene polymer compositions containing high melt strength propylene polymer material |
| US5443898A (en) * | 1993-06-29 | 1995-08-22 | Fiberweb North America, Inc. | Nonwoven webs and method of making same |
| WO1996003444A1 (en) * | 1994-07-21 | 1996-02-08 | Akzo Nobel N.V. | Modification of (co)polymers with cyclic ketone peroxides |
| US5594074A (en) * | 1995-02-21 | 1997-01-14 | Shell Oil Company | Process for improving processability of ultra low melt viscosity polymer |
| US6060584A (en) * | 1998-05-13 | 2000-05-09 | Eastman Chemical Company | Process for the degradation of polyolefins |
| KR100330308B1 (en) * | 1999-06-29 | 2002-04-01 | 이영일 | Polypropylene resin composition having high melting tension |
| US6433133B1 (en) | 1999-11-16 | 2002-08-13 | Eastman Chemical Company | Process for reducing the weight average molecular weight and melt index ratio of polyethylenes and polyethylene products |
| US20040159972A1 (en) * | 2000-08-04 | 2004-08-19 | Koschmieder Stefan U. | Propylene polymers having agreeable odor characteristics and shaped articles thereof |
| EP1186618A1 (en) * | 2000-09-08 | 2002-03-13 | ATOFINA Research | Controlled rheology polypropylene heterophasic copolymers |
| US6503990B2 (en) * | 2001-01-12 | 2003-01-07 | Atofina Chemicals, Inc. | Safe, efficient, low t-butanol forming organic peroxide for polypropylene modification |
| US6610792B2 (en) | 2001-07-26 | 2003-08-26 | Fina Technology, Inc. | Polypropylene copolymers and method of preparing polyproylene copolymers |
| EP1312617A1 (en) * | 2001-11-14 | 2003-05-21 | ATOFINA Research | Impact strength polypropylene |
| BRPI0411153A (en) * | 2003-06-05 | 2006-07-11 | Cuno Inc | process of obtaining filter elements using polyolefins having certain rheological properties and products obtained |
| US7255012B2 (en) * | 2004-12-01 | 2007-08-14 | Rosemount Inc. | Process fluid flow device with variable orifice |
| EP1847555A1 (en) * | 2006-04-18 | 2007-10-24 | Borealis Technology Oy | Multi-branched Polypropylene |
| WO2009058477A1 (en) | 2007-10-31 | 2009-05-07 | Exxonmobil Chemical Patents Inc. | Polypropylene spunbond fibers |
| US9333716B2 (en) * | 2007-12-20 | 2016-05-10 | Novartis Ag | Method for cast molding contact lenses |
| EP2096197A1 (en) | 2008-02-27 | 2009-09-02 | ExxonMobil Chemical Patents Inc. | Polypropylene spunbond fibers |
| US20100324225A1 (en) * | 2009-06-23 | 2010-12-23 | Michael Zummallen | Controlled-Rheology Polypropylene |
| KR102022307B1 (en) | 2013-04-30 | 2019-09-18 | 도레이첨단소재 주식회사 | Polypropylene spunbond nonwoven fabric and preparing method thereof |
| WO2015085390A2 (en) * | 2013-12-13 | 2015-06-18 | Braskem S.A. | Method for producing controlled rheology polypropylene, polypropylene, use thereof and manufactured articles |
| KR20160101953A (en) | 2013-12-19 | 2016-08-26 | 다우 글로벌 테크놀로지스 엘엘씨 | Process to visbreak propylene-based polymers with c-c initiators |
| RU2679146C2 (en) | 2014-03-11 | 2019-02-06 | Акцо Нобель Кемикалз Интернэшнл Б.В. | Cyclic ketone peroxide composition |
| EP3620475A1 (en) | 2018-09-06 | 2020-03-11 | Evonik Operations GmbH | Amorphous poly-alfa-olefins and their use in hot melt compositions with improved sprayability |
| WO2024170554A1 (en) * | 2023-02-14 | 2024-08-22 | Totalenergies Onetech | Polypropylene composition for injection molding |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3144436A (en) * | 1961-01-04 | 1964-08-11 | Du Pont | Process for degrading stereoregular polymers |
| US3862265A (en) * | 1971-04-09 | 1975-01-21 | Exxon Research Engineering Co | Polymers with improved properties and process therefor |
| JPS5148196B2 (en) * | 1972-03-11 | 1976-12-18 | ||
| US3940379A (en) * | 1973-05-21 | 1976-02-24 | Dart Industries, Inc. | Process for controlled degradation of propylene polymers |
| US4271279A (en) * | 1975-06-30 | 1981-06-02 | Argus Chemical Corporation | Cyclic perketals and their use for cross-linking high density polyethylene |
| CA1210176A (en) * | 1981-06-15 | 1986-08-19 | Michael T. Morman | Degradation of polypropylene for future improved processability |
| US4451589A (en) * | 1981-06-15 | 1984-05-29 | Kimberly-Clark Corporation | Method of improving processability of polymers and resulting polymer compositions |
-
1986
- 1986-05-06 US US06/860,356 patent/US4707524A/en not_active Expired - Fee Related
-
1987
- 1987-04-17 EP EP87903117A patent/EP0270570A1/en not_active Withdrawn
- 1987-04-17 WO PCT/US1987/000852 patent/WO1987006944A1/en not_active Application Discontinuation
- 1987-04-17 JP JP62502556A patent/JPH07121966B2/en not_active Expired - Lifetime
- 1987-04-27 ZA ZA873001A patent/ZA873001B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63503228A (en) | 1988-11-24 |
| US4707524A (en) | 1987-11-17 |
| ZA873001B (en) | 1987-12-30 |
| WO1987006944A1 (en) | 1987-11-19 |
| EP0270570A1 (en) | 1988-06-15 |
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